Toxiferine

Toxiferine
Clinical data
Other names	C-Toxiferine I C-Toxiferin I Toxiferine I
Identifiers
	IUPAC name (2E)-2-[(1S,9Z,11S,13S,14S,17S,25Z,27S,30S,33S,35S,36S,38E)-38-(2-hydroxyethylidene)-14,30-dimethyl-8,24-diaza-14,30-diazoniaundecacyclo[25.5.2.211,14.11,26.110,17.02,7.013,17.018,23.030,33.08,35.024,36]octatriaconta-2,4,6,9,18,20,22,25-octaen-28-ylidene]ethanol;
CAS Number	6888-23-9;302-30-7;
PubChem CID	5281411;
ChemSpider	4444760;
UNII	9M7D9K3OJI;
ChEMBL	ChEMBL231047;
CompTox Dashboard (EPA)	DTXSID30897243 ;
Chemical and physical data
Formula	C40H46N4O2
Molar mass	614.834 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [H][C@@]12[C@@]3(CC[N+]2(C)C/C4=C/CO)[C@@]5([H])N(C6=C3C=CC=C6)/C=C7[C@]([C@@]8(CC[N+]9(C)C/%10)[C@]9([H])C[C@]\7([H])C%10=C/CO)([H])N(C%11=C8C=CC=C%11)/C=C5/[C@]4([H])C1;
	InChI InChI=1S/C40H46N4O2/c1-43-15-13-39-31-7-3-5-9-33(31)41-22-30-28-20-36-40(14-16-44(36,2)24-26(28)12-18-46)32-8-4-6-10-34(32)42(38(30)40)21-29(37(39)41)27(19-35(39)43)25(23-43)11-17-45/h3-12,21-22,27-28,35-38,45-46H,13-20,23-24H2,1-2H3/q+2/b25-11-,26-12-,29-21-,30-22-/t27-,28-,35-,36-,37-,38-,39+,40+,43-,44-/m0/s1;

Toxiferine, also known as c-toxiferine I, is one of the most toxic plant alkaloids known. It is derived from several plant species, including Strychnos toxifera. Historically, it has been used as an arrow poison by indigenous peoples in South America for its neuromuscular blocking properties, allowing them to paralyze animals during hunting, but also possibly kill due to paralysis of the respiratory muscles. Toxiferine functions as an acetylcholine receptor (AChR) antagonist. The paralysis caused by toxiferine can in turn be antagonized by neostigmine.

Toxiferine is the most important component in calabash curare. Curare poisons contain many different toxins with similar properties of toxiferine. The most well known component of curare is tubocurarine. The paralysis caused by toxiferine is very similar to that caused by tubocurarine, however toxiferine is ~170 times as potent. The preparation of curare poisons involves complex rituals wherein the tribes extract toxins from various plants.